NEW YORK—Shortly after he got on the stand, prosecutors handed FBI agent Tom Kiernan an item called Government's Exhibit 200. It was a Samsung 700z laptop wrapped in thick plastic wrap. Kiernan removed it, not without some difficulty, and inspected it.

Yes, Kiernan told prosecutor Timothy Howard, this was the computer he and two other federal agents had taken from Ross Ulbricht in October 2013. It was a prize so important they literally snatched it out from underneath him, before they even arrested Ulbricht.

On that day, a male and female agent started an argument in San Francisco's Glen Park public library, to get Ulbricht's attention. As soon as Ulbricht was distracted, another agent grabbed the open computer and gave it to Kiernan, who is an FBI computer specialist. Kiernan spent the next three hours doing "triage" on the machine. Without allowing it to go idle, and thus become encrypted, he took photographs, went through the browser history, and ultimately handed it off to another agent who imaged the hard drive.

Today, with Kiernan on the stand offering confirmation, Howard walked the jury through the enormous amount of data pulled from Ulbricht's computer. Defense lawyers haven't had a chance yet to respond to this evidence—that will likely come tomorrow. The mountain they have to climb looks higher than ever, though. Last week, Ulbricht's lawyer outlined a defense in which Ulbricht walked away from the marketplace he created and was "lured back." But what will explain the dozens of folders of data on this laptop, with data from the upper echelons of Silk Road management—mixed with the most intimate details of Ulbricht's personal life?

The jury saw spreadsheets of Silk Road finances, Ulbricht's personal tracking of his "net worth," and got just a small glimpse of the years of TorChat chat logs with Silk Road administrators that were on the machine. In those chats, "myself"—the default name for a user of TorChat—made key executive decisions about how to run Silk Road.

There were many decisions that had to be made: promotions and demotions, contests and castigations. The jury saw Silk Road org charts, payroll documents, and daily logs tracking staff activities. They saw Ulbricht's old passport and driver's license, and the scanned IDs of Silk Road admins.

The computer also contained what prosecutors say is Ulbricht's personal journal. It goes back to 2010, in which Ulbricht describes his early plans to create Silk Road and seed it by growing psychedelic mushrooms, and selling them for cheap. He describes his personal goals and his days spent working, surfing, or drinking with friends. He also describes half-truths told to friends, and the pain that brought.

That diary was read into the public record today. It mentions several people who appear to be friends of Ulbricht, but their roles are unknown.

"I went out with Jessica," said Howard, reading Ulbricht's diary into the public record in a rote monotone. "Our conversation was somewhat deep. I felt compelled to reveal myself to her... It was terrible. I told her I have secrets."

"Creating a year of prosperity and power"

The journal on Ulbricht's computer only seems to have been kept occasionally. Howard read parts of four entries out loud today, which were also shown on a screen in court.

In the first, Ulbricht writes about dissatisfaction with his life that led him towards building the site. He'd been working for a company called "Good Wagon Books" in Austin, an online used-book recycling business started by his partner Donny (no last name given). The diary read:

Donny and I had worked on it the last quarter of 2009 and were trying to ramp up by hiring people to go door-to-door. It was a real struggle and by the end of our trial partnership, it was clear that we hadn’t grown the business to the point that it made sense for me to stay on... There I was, with nothing. My investment company came to nothing, my game company came to nothing, Good Wagon came to nothing, and then this.

I had to find a job quickly, so I turned to Craig’s List and found American Journal Experts. For the next six months, I edited scientific papers written by foreigners. It sucked. The hours were flexible, but it drained me. I hated working for someone else and trading my time for money with no investment in myself.

Ulbricht kept up with Good Wagon Books, taking over when Donny moved on to become an executive at a milling company in Dallas. He started early work on Silk Road at about the same time. It took a toll on his personal life. He wrote:

While all of this was happening, I began working on a project that had been in my mind for over a year. I was calling it Underground Brokers, but eventually settled on Silk Road. The idea was to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them. I had been studying the technology for a while, but needed a business model and strategy. I finally decided that I would produce mushrooms so that I could list them on the site for cheap to get people interested. I worked my ass off setting up a lab in a cabin out near Bastrop off the grid. In hindsight, this was a terrible idea and I would never repeat it, but I did it and produced several kilos of high quality shrooms. On the website side, I was struggling to figure out on my own how to set it up. Driving out to Bastrop, working on Good Wagon, and trying to keep up my relationship with Julia was taking all of my time. By the end of the year, I still didn’t have a site up, let alone a server.

I went through a lot over the year in my personal relationships as well. I had mostly shut myself off from people because I felt ashamed of where my life was. I had left my promising career as a scientist to be an investment adviser and entrepreneur and came up empty handed. More and more my emotions and thoughts were ruling my life and my word was losing power. At some point I finally broke down and realized my love for people again, and started reaching out. Throughout the year I slowly re-cultivated my relationship with my word and started honoring it again.

My relationship with Julia was pretty rocky throughout the year. We even broke up for about a month and half toward the end. I couldn’t even tell you now why it was a struggle, or why we broke up. On my side, I wasn’t communicating well at all. I would let little things build up until I got mad. We eventually got back together and even moved in together, and it has been amazingly good since.

In 2011, I am creating a year of prosperity and power beyond what I have ever experienced before. Silk Road is going to become a phenomenon and at least one person will tell me about it, unknowing that I was its creator. Good Wagon Books will find its place and get to the point that it basically runs itself. Julia and I will be happy and living together. I have many friends I can count on who are powerful and connected.

"Tried to tell the truth without revealing the bad part"

The second journal entry was the longest. The file is called simply "2011," and was last modified in February of 2012. It's a narrative of Ulbricht creating the site, growing and selling mushrooms, and getting his first sales. He wrote:

[S]till working on good wagon books and Silk Road at the same time. Programming now. Patchwork php mysql. Don't know how to host my own site. Didn't know how to run bitcoind. Got the basics of my site written. Launched it on freedomhosting. Announced it on the bitcointalk forums. Only a few days after launch, I got my first signups, and then my first message. I was so excited I didn't know what to do with myself. Little by little, people signed up, and vendors signed up, and then it happened. My first order. I'll never forget it.

The next couple of months, I sold about 10 lbs of shrooms through my site. Some orders were as small as a gram, and others were in the qp range. Before long, I completely sold out. Looking back on it, I maybe should have raised my prices more and stretched it out, but at least now I was all digital, no physical risk anymore. Before long, traffic started to build. People were taking notice, smart, interested people. Hackers. For the first several months, I handled all of the transactions by hand.... Between answering messages, processing transactions, and updating the codebase to fix the constant security holes, I had very little time left in the day, and I had a girlfriend at this time!

After that, Ulbricht describes re-writing the site's code, "the most stressful couple of months I've ever experienced." The weekend of switching to the new code was "the peak of stress for me," he wrote. Around the same time, the Silk Road became famous. He wrote:

[I]n addition to these stressors, Silk Road got its first press, the infamous Gawker article. When you look at the historical #s, you can see right when it happened. A huge spike in signups, and the beginning of an upward trend in commerce that would continue until the time of this writing, and hopefully for much longer...

Most interestingly, two US senators came out against the site and against bitcoin. They made a big deal out of it and called for a shutdown of the site. I started to get into a bad state of mind. I was mentally taxed, and now I felt extremely vulnerable and scared. The US govt, my main enemy was aware of me and some of it's members were calling for my destruction. This is the biggest force wielding organization on the planet...

Most importantly, the market began it's path to maturity. Vendors and buyers forged great relationships, more vendors came in to fill holes in the market, others competed and variety, customer service, and professionalism emerged. After making about $100k and up to a good $20-25k monthly, I decided it was time to bring in some hired guns to help me take the site to the next level.

He talks about staff decisions and different types of employees: "SYG, the schmoozer who winds up being a waste, DA, the model employee. Super enthusiastic, hard working, and trainable. Then there is utah, professional who does it for the money. Get's [sic] the job done, but his heart isn't always in it."

Later in 2011, a new personality came to the site.

Around this time, Variety Jones showed up. This was the biggest and strongest willed character I had met through the site thus far. He quickly proved to me that he had value by pointing out a major security hole in the site I was unaware of... He has advised me on many technical aspect of what we are doing, helped me speed up the site and squeeze more out of my current servers. He also has helped me better interact with the community around Silk Road, delivering proclamations, handling troublesome characters, running a sale, changing my name, devising rules, and on and on. He also helped me get my head straight regarding legal protection, cover stories, devising a will, finding a successor, and so on. He's been a real mentor.

The third journal entry was a file called "daily.odt," a short paragraph created on Dec. 29, 2011. The first part is VJ giving more advice:

Chatted with VJ again today. Him coming onto the scene has re inspired me and given me direction on the SR project. He has helped me see a larger vision. A brand that people can come to trust and rally behind. Silk Road chat, Silk Road exchange, Silk Road credit union, Silk Road market, Silk Road everything! And it's been amazing just talking to a guy who is so intelligent and in the same boat as me, to a certain degree at least. So, today we talked mostly about the exchange, what to charge, boundary conditions, etc.

The same entry moves on to some deep conversations, that were later regretted. Ulbricht wrote:

Then I went for a surf with Billy Becket. Caught a couple of good waves, chatted with him took some wipe outs, and went in. Soon after, I ran around the city with Ashely and Kelly. We drank some beer, walked around the city and botanical gardens. I then went out with Jessica. Our conversation was somewhat deep. I felt compelled to reveal myself to her. It was terrible. I told her I have secrets. She already knows I work with bitcoin wich is also terrible. I'm so stupid. Everyone knows I am working on a bitcoin exchange. I always thought honesty was the best policy, and now I don't know what to do. I should've just told everyone I am a freelance programmer or something, but I had to tell half truthes. It felt wrong to lie completely so I tried to tell the truth without revealing the bad part, but now I am in a jam. Everyone knows too much. Dammit.

“I've been incredibly blessed”

In a folder labeled "TorChat," Ulbricht's computer holds years' worth of chat logs. The TorChat program that creates logs describing the primary user as "myself." Ulbricht says he wasn't the Dread Pirate Roberts, the identity who ran the Silk Road drug marketplace. But whoever was "myself" on his computer's chat logs did admit—boasted, even—that he ran the show.

The first chat shown to the jury was from April of 2012:

sSh: greetings

myself: hi there

myself: what's up?

sSh: may i ask to whom i'm speaking? a formality of course

myself: DPR, and you are?

sSh: this is squid

myself: why do you keep changing identities?

sSh: i've figured it out so that this will be my permanent ID.

myself: sounds good. what have you been up to?

A journal entry found on Ulbricht's computer describes Digital Alchemy as the one he hired to be a "right hand man." In a January 2012 chat, "myself" told Digital Alchemy, a Silk Road staffer, that he'd be taking on an important new responsibility—handling vendors who don't follow the rules.

"are you ready to become judge jury and executioner?" messaged DPR (writing as "myself," the term used in all these chat logs).

"yep :)" wrote back a user named DigitalAlch.

Later, DPR told Digital Alchemy he'd have to change his name, since there was too much Silk Road forum activity under his current name.

There are nearly 1,100 pages of chat logs with "vj," apparently Variety Jones, who Ulbricht identifies as his mentor. Page 312 of that log reads in part:

myself: this whole thing has been on a wing and a prayer. besides basic php and html, i've learned everything on the fly.

vj: just thank fsm

myself: fsm?

vj: $deity

myself: ahhh

myself: i've been incredibly blessed. i was a hair's breadth from going to jail before the site even launched.

Later, Variety Jones changed his identity to cimon. "Variety Jones is dead," he wrote in a chat to DPR. "Poor fella. No more seed biz for him." On Oct. 24, 2012, "myself" asked cimon for suggestions about recruiting:

myself: right now i'm spending an hour a day on resolutions and inigo (new guy) is dealing w/ messages

myself: i might try recruiting at bitcointalk.org

cimon: dude, really?

myself: well, working for a criminal enterprise isn't exactly enticing

The "myself" identity meted out punishment, too. He told cimon that between one and three vendors got "demoted" each week. The most common offenses were faking feedback, going outside of the Silk Road escrow system, or selling fake product.

“We are bringing order and civility”

Dread Pirate Roberts did the hiring and firing on Silk Road, and each hire had to send their scanned ID with current address. "it will be stored encrypted," DPR explained to one interviewee. "i'll probably never need to decrypt it."

"that's a big trust," answered cp, the recruit.

"yes it is."

Ulbricht's computer had encrypted pictures of staffers on it. Kiernan broke the encryption. Today, the jury saw one ID: the Virginia driver's license of Andrew Michael Jones, a.k.a. inigo, the man hired to manage message forums. Jones was from Norfolk, born in 1984. He called himself "Patrick Henry" in one chat:

myself: its a substance and we want to err on the side of not restricting things

inigo: this is the black market after all :)

myself: it is, and we are bringing order and civility to it

In early 2013, DPR chatted with "scout," a seller account that would later be taken over by a Homeland Security investigator. Scout was being recruited to join Silk Road as staff, but she was scared. Their chat read, in part:

myself: why do you still have reservations?

scout: the only reservation I have is about the safety of being on staff.

myself: the way i get over it is looking at the risk/reward ratio.

myself: when you look at the chance of getting caught, its incredibly small

myself: put yourself in the shoes of a prosecutor trying to build a case

The only way the authorities could build such a case, DPR explained, would be by getting unencrypted information about Silk Road—a virtual impossibility, he assured scout.

It was a surreal moment. Prosecutor Timothy Howard and his colleagues had built the case that DPR had said couldn't be built, and were reading his dares back to a jury. Howard read the chats into the record in a staccato rhythm, as Kiernan confirmed each exhibit.

The men had not broken the encryption. After seeing Ulbricht in public, they quickly scuttled their original plan, to arrest him at home the following day. They adopted a more street-level approach. It was one their suspect—a young man with two college degrees, hunting for a spot in a San Francisco cafe, coming to rest in a quiet library—had not thought of. It was the strategy of the poor and the desperate, of thieves and thugs.